Indeno(1,2,3-ij)(2,7)naphthyridine

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  • Identifiers

    CAS number
    58786-39-3

    Molecular formula
    C14H8N2

    SMILES
    C1=CC=C2C(=C1)C3=NC=CC4=C3C2=NC=C4

    Safety labels

  • Odor profile

    Fragrance
    Floral 60.54%
    Animal 49.77%
    Fruity 41.52%
    Musty 29.55%
    Neroli 28.26%
    Burnt 28.05%
    Earthy 27.08%
    Pungent 26.18%
    Cheesy 24.97%
    Grape 24.46%

     

    Flavor
    Bitter 96.2%
    Very strong 18.9%
    Indole 18.15%
    Moth ball 17.16%
    Cereal 17.05%
    Animal 16.7%
    Naphthelene 16.47%
    Rotten 16.28%
    Nitrile 16.28%
    Cedarleaf 15.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    4.86 (weak acid)

    Molecular weight
    204.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    441°C

    Melting point expt.

    • 156 - 157 °C

    Flash point

    • 194.49 ˚C est.

  • Synonyms

    • Eupolauridine
    • 58786-39-3
    • Indeno(1,2,3-ij)(2,7)naphthyridine
    • M3LXQ9G7MF
    • Indeno[1,2,3-ij][2,7]naphthyridine
    • DTXSID80974311
    • 2,8-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-1,3,5(16),6,8,10,12,14-octaene
    • 2,8-diazatetracyclo(7.6.1.05,16.010,15)hexadeca-1,3,5(16),6,8,10,12,14-octaene
    • 2,8-diazatetracyclo(7.6.1.0^(5,16).0^(10,15))hexadeca-1,3,5,7,9(16),10(15),11,13-octaene
    • 2,8-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-1,3,5,7,9(16),10(15),11,13-octaene
    • RefChem:139508
    • DTXCID201401740
    • Canangine
    • 1,6-Diazafluoranthene
    • CHEBI:67605
    • Eupolauridin
    • EL Base 1
    • UNII-M3LXQ9G7MF
    • CHEMBL477708
    • orb3023956
    • SCHEMBL3125284
    • BDBM50202838
    • DB-225986
    • Q5851990
    • 2,8-DIAZATETRACYCLO(7.6.1.05,16.010,15)HEXADECA-1,3,5,7,9(16),10,12,14-OCTAENE
    • 58786-39-3

  • Applications

    Indeno(1,2,3-ij)(2,7)naphthyridine (CAS 58786-39-3) is primarily encountered as a synthetic intermediate and building block for nitrogen-containing polycyclic heterocycles in medicinal chemistry research. It is commonly evaluated as a scaffold for designing pharmacologically active compounds and as a precursor in the development of related heteroaromatic libraries. The rigid polycyclic core also motivates exploration as a building block in materials science, including exploratory work for organic electronics and polymer precursors. Additionally, it may be used as a dye or pigment precursor in specialty coatings/inks, and is sometimes investigated in agrochemical research where heteroaromatic frameworks are relevant. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.12
    methanol 5.88
    isopropanol 7.26
    water 0.04
    ethyl acetate 28.07
    n-propanol 10.1
    acetone 35.48
    n-butanol 9.57
    acetonitrile 11.99
    DMF 118.98
    toluene 27.31
    isobutanol 8.99
    1,4-dioxane 49.03
    methyl acetate 29.66
    THF 89.39
    2-butanone 30.01
    n-pentanol 11.81
    sec-butanol 6.95
    n-hexane 3.05
    ethylene glycol 5.02
    NMP 121.45
    cyclohexane 5.7
    DMSO 72.1
    n-butyl acetate 35.37
    n-octanol 16.32
    chloroform 94.8
    n-propyl acetate 30.01
    acetic acid 15.85
    dichloromethane 122.57
    cyclohexanone 77.19
    propylene glycol 3.71
    isopropyl acetate 21.33
    DMAc 87.11
    2-ethoxyethanol 19.92
    isopentanol 10.1
    n-heptane 7.03
    ethyl formate 34.84
    1,2-dichloroethane 93.59
    n-hexanol 21.07
    2-methoxyethanol 26.27
    isobutyl acetate 25.07
    tetrachloromethane 21.25
    n-pentyl acetate 36.63
    transcutol 31.45
    n-heptanol 18.32
    ethylbenzene 24.0
    MIBK 22.19
    2-propoxyethanol 33.84
    tert-butanol 8.95
    MTBE 8.18
    2-butoxyethanol 27.97
    propionic acid 15.62
    o-xylene 22.27
    formic acid 5.07
    diethyl ether 14.59
    m-xylene 21.98
    p-xylene 32.11
    chlorobenzene 47.23
    dimethyl carbonate 33.17
    n-octane 5.29
    formamide 13.23
    cyclopentanone 102.75
    2-pentanone 28.89
    anisole 30.66
    cyclopentyl methyl ether 39.63
    gamma-butyrolactone 122.9
    1-methoxy-2-propanol 18.52
    pyridine 77.92
    3-pentanone 29.09
    furfural 107.28
    n-dodecane 4.45
    diethylene glycol 27.22
    diisopropyl ether 7.05
    tert-amyl alcohol 7.9
    acetylacetone 45.39
    n-hexadecane 5.22
    acetophenone 44.18
    methyl propionate 32.93
    isopentyl acetate 33.69
    trichloroethylene 151.93
    n-nonanol 16.44
    cyclohexanol 15.26
    benzyl alcohol 29.13
    2-ethylhexanol 20.46
    isooctanol 16.47
    dipropyl ether 23.45
    1,2-dichlorobenzene 53.63
    ethyl lactate 19.32
    propylene carbonate 67.73
    n-methylformamide 35.48
    2-pentanol 6.76
    n-pentane 2.49
    1-propoxy-2-propanol 24.03
    1-methoxy-2-propyl acetate 35.46
    2-(2-methoxypropoxy) propanol 24.95
    mesitylene 15.75
    ε-caprolactone 64.43
    p-cymene 22.97
    epichlorohydrin 114.35
    1,1,1-trichloroethane 55.02
    2-aminoethanol 7.1
    morpholine-4-carbaldehyde 86.96
    sulfolane 137.84
    2,2,4-trimethylpentane 1.71
    2-methyltetrahydrofuran 46.99
    n-hexyl acetate 35.18
    isooctane 1.71
    2-(2-butoxyethoxy)ethanol 29.43
    sec-butyl acetate 20.24
    tert-butyl acetate 20.68
    decalin 5.82
    glycerin 9.07
    diglyme 62.16
    acrylic acid 19.13
    isopropyl myristate 19.57
    n-butyric acid 22.13
    acetyl acetate 23.95
    di(2-ethylhexyl) phthalate 22.13
    ethyl propionate 28.56
    nitromethane 37.59
    1,2-diethoxyethane 27.4
    benzonitrile 43.71
    trioctyl phosphate 18.8
    1-bromopropane 34.21
    gamma-valerolactone 103.09
    n-decanol 13.95
    triethyl phosphate 24.03
    4-methyl-2-pentanol 6.52
    propionitrile 18.46
    vinylene carbonate 70.07
    1,1,2-trichlorotrifluoroethane 62.46
    DMS 39.62
    cumene 19.83
    2-octanol 13.76
    2-hexanone 30.5
    octyl acetate 24.12
    limonene 24.33
    1,2-dimethoxyethane 53.47
    ethyl orthosilicate 21.28
    tributyl phosphate 19.92
    diacetone alcohol 23.62
    N,N-dimethylaniline 31.35
    acrylonitrile 29.69
    aniline 23.92
    1,3-propanediol 9.87
    bromobenzene 54.73
    dibromomethane 77.08
    1,1,2,2-tetrachloroethane 99.53
    2-methyl-cyclohexyl acetate 31.81
    tetrabutyl urea 31.07
    diisobutyl methanol 12.37
    2-phenylethanol 36.64
    styrene 24.55
    dioctyl adipate 28.25
    dimethyl sulfate 55.63
    ethyl butyrate 32.91
    methyl lactate 19.0
    butyl lactate 24.79
    diethyl carbonate 28.14
    propanediol butyl ether 15.83
    triethyl orthoformate 25.3
    p-tert-butyltoluene 18.26
    methyl 4-tert-butylbenzoate 39.39
    morpholine 42.25
    tert-butylamine 6.04
    n-dodecanol 12.14
    dimethoxymethane 61.05
    ethylene carbonate 55.72
    cyrene 41.28
    2-ethoxyethyl acetate 40.51
    2-ethylhexyl acetate 30.7
    1,2,4-trichlorobenzene 59.15
    4-methylpyridine 59.19
    dibutyl ether 21.12
    2,6-dimethyl-4-heptanol 12.37
    DEF 49.29
    dimethyl isosorbide 56.91
    tetrachloroethylene 83.75
    eugenol 37.63
    triacetin 35.75
    span 80 22.38
    1,4-butanediol 7.45
    1,1-dichloroethane 45.38
    2-methyl-1-pentanol 13.12
    methyl formate 39.98
    2-methyl-1-butanol 9.24
    n-decane 6.26
    butyronitrile 19.54
    3,7-dimethyl-1-octanol 13.54
    1-chlorooctane 21.23
    1-chlorotetradecane 10.46
    n-nonane 5.91
    undecane 5.21
    tert-butylcyclohexane 4.59
    cyclooctane 3.29
    cyclopentanol 22.0
    tetrahydropyran 39.33
    tert-amyl methyl ether 9.79
    2,5,8-trioxanonane 45.94
    1-hexene 10.21
    2-isopropoxyethanol 17.58
    2,2,2-trifluoroethanol 13.12
    methyl butyrate 39.9

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction